Phosphinylidynetrimethanol

• CAS: 1067-12-5
• Catalog Number: ACM1067125
• Category: Main Products
• Molecular Weight: 124.08
• Molecular Formula: C3H9O3P
• Synonyms: Tris(hydroxymethyl)phosphine oxide
• Appearance: Light green or colorless transparent liquid
• Physical State: Liquid

Case Study

Tris(hydroxymethyl)phosphine Oxide Used in the Preparation of Phosphine Oxide-containing Hyperbranched Polyols

Ma, Chao, et al. Chemical Engineering Journal, 2022, 431, 133347.

Using tris(hydroxymethyl)phosphine oxide (THPO) as raw material, a new type of phosphine oxide-containing hyperbranched polyol (POCHP) can be synthesized through condensation polymerization. The prepared POCHP and/or expandable graphite (EG) can be further incorporated into rigid polyurethane foam (RPUF) to improve the flame retardant properties of RPUF. In this work, condensation polymers were first prepared by sequential polyesterification of phthalic anhydride and THPO. Then, POCHP was synthesized through a ring-opening reaction between the condensation polymer and 1,2-propylene oxide.
Improved flame retardancy through POCHP and EG
· ERPUF50 obtained by adding POCHP and EG exhibits excellent fire safety. It has a limiting oxygen index of 30.0% and a UL-94 V-0 rating.
· Through the dual-phase flame retardant mechanism, the peak heat release, total heat release and total smoke emission of ERPUF50 were reduced by 71.1%, 52.2% and 71.1% respectively.
· The combination of POCHP and EG significantly reduces the production of CO and NOx during RPUF combustion.

Tris(Hydroxymethyl)Phosphine Oxide-Derived Acyclic Nucleoside Analogues Conjugated to DNA Nucleobases

Nawrot, Barbara, et al. Antiviral Chemistry and Chemotherapy, 2004, 15(6), 319-328.

The development of new more active or selective antiviral agents involves various base or alkyl side chain modifications. Tris(hydroxymethyl)phosphine oxide (THPO) or bis(hydroxymethyl)phosphinic acid (BHPA) can serve as scaffolds for alkyl side chains coupled to DNA nucleobases or 5-fluorouracil. A series of acyclic nucleoside analogs were synthesized, including guanine derivatives of THPO.
Coupling of nucleobases with a THPO residue
· Two OH functions of tris-(hydroxymethyl)phosphine oxide [4] were selectively protected with 4,4'-dimethoxytrityl (DMT) groups by the reaction with 2 equivalents of DMTCl.
· The third OH group was activated in the presence of 4-N,N-dimethylaminopyridine (DMAP) with ptoluenesulphonyl chloride resulting in formation of [6].
· Compound [5] was used as a substrate for a Mitsunobu reaction performed with N-3-benzoylthymine, non-protected adenine, with N-2-isobutyryl-O6-diphenylcarbamoylguanine and with N-3-benzoyl-5- fluorouracil.
· Triphenylphosphine (PPh3)- and diisopropyl azodicarboxylate (DIAD)-assisted coupling reactions gave derivatives [7a,c,d] and [7e], respectively.
· While thymine and uracil could be substituted exclusively at the N-1 position (the N-3 position was protected with a benzoyl group), the N-2,O-6-protected guanine afforded two products in a ratio of 95:5; the predominant one was established to have structure [7d].

Custom Q&A

What is the molecular formula of the compound?

The molecular formula is C3H9O4P.

What are the synonyms for the compound?

The synonyms for the compound are tris(hydroxymethyl)phosphine oxide, methanol, phosphinylidynetris-, trimethylolphosphine oxide, and bis(hydroxymethyl)phosphorylmethanol.

What is the molecular weight of the compound?

The molecular weight of the compound is 140.07 g/mol.

How was the molecular weight computed?

The molecular weight was computed by PubChem 2.1.

When was the compound created?

The compound was created on March 26, 2005.

When was the compound last modified?

The compound was last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is bis(hydroxymethyl)phosphorylmethanol.

What is the InChI of the compound?

The InChI of the compound is InChI=1S/C3H9O4P/c4-1-8(7,2-5)3-6/h4-6H,1-3H2.

What is the InChIKey of the compound?

The InChIKey of the compound is MRVZORUPSXTRHD-UHFFFAOYSA-N.

What is the canonical SMILES of the compound?

The canonical SMILES of the compound is C(O)P(=O)(CO)CO.